Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines
Zi, Quanxing; Li, Minyan; Cong, Jielun; Deng, Guogang; Duan, Shengzu; Yin, Meng; Chen, Wen; Jing, Hong; Yang, Xiaodong*; Walsh, Patrick J*
Organic Letters
Volume:24 Issue:9 Pages:1786-1790
DOI:10.1021/acs.orglett.2c00140
Published: 2022-Mar-11
https://pubs.acs.org/doi/10.1021/acs.orglett.2c00140
Abstract
Herein is introduced the application of "super-electron-donor"(SED) 2-azaallyl anions in a tandem reduction/radical cyclization/radical coupling/aromatization protocol that enables the rapid construction of isoquinolines. The value of this transition-metal-free method is highlighted by the wide range of isoquinoline ethyl amines prepared with good functional group tolerance and yields. An operationally simple gram scale synthesis is also conducted, confirming the scalability.
